


Cherri's Room

by TheNightWaffle



Category: Undertale (Video Game)
Genre: Alternate Universe - Underfell (Undertale), Ecto-Genitalia (Undertale), Ecto-Vagina (Undertale), Fluff, Fluff and Smut, Light Dom/sub, Lingerie, Oral Sex, Prostitution, Smut, Sub Sans (Undertale), Underfell Papyrus (Undertale), Underfell Sans (Undertale)
Language: English
Status: Completed
Published: 2019-12-18
Updated: 2019-12-18
Packaged: 2021-02-25 21:02:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,260
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21851875
Author URL: https://archiveofourown.org/users/TheNightWaffle/pseuds/TheNightWaffle
Summary: A brothel. You couldn’t believe out of all the places Papyrus would have sent you to talk some sense into his brother, it was at a brothel.
Relationships: Papyrus (Undertale) & Reader, Sans (Undertale)/Reader
Comments: 18
Kudos: 179





	Cherri's Room

**Author's Note:**

> I need to get back to my main works but I really wanted to write this. Oof.

There it was. 

In the dingiest, most dangerous part of town was the unmarked building widely known amongst the skeevers and freaks as the Angel’s Den. 

Inside, the carpet looked like it came straight out of a 70s porno. It was filthy, the gaudiest thing you had ever seen, and even worse, the chairs matched. The walls, other than the peeling dark green wallpaper, were completely bare. The only other person in the room seemed to be a balding man with a stained wife-beater sitting behind the counter.

A brothel. You couldn’t believe out of all the places Papyrus would have sent you to talk some sense into his brother, it was at a brothel. 

You approached the man, feeling very out of place in your pantsuit, and he regarded you with apt interest.

“Hello, sweetcheeks,” he purred. You resisted the urge to gag, “Now what can I do for you? Here to apply for a job?”

“Actually,” you began, keeping a carefully straight face, “I’m here to make an appointment with one of your workers.”

His lecherous grin spread further across his face, but a harsh glare stopped him from saying whatever it was he was about to say. Merely chuckling to himself, he opened the catalogue on the counter and turned it to face you,

“Take your pick, sugar tits, and we’ll get right on making that ‘appointment’. The base price per hour is written beside each picture.”

This is not how you thought your day would go when you left for work that morning.

Looking for someone in particular, you flipped through the book, scanning the pictures. You couldn’t help but note that there was a significantly higher number of human workers than monster workers. As in, there are only two monster workers and one of them was a bird of some sort while the other one was a skeleton. There, at the back of the book and under the name Cherri, you found the skeleton you were looking for. In his photo, he had a full, red female ecto-body and was smiling teasingly at the camera. A pink silk robe hung off his form, leaving just enough to the imagination.

Not wanting to give away your connection to Sans, you carefully schooled your expression, simply tapping his photo,

“Her.”

The clerk glanced at your choice, looking absolutely delighted,

“A lesbian and a freak? You sure you won’t reconsider that job offer, Baby Cakes?”

Shooting him a disgusted look, you replied curtly,

“Quite.”

He shrugged and handed you a key,

“Whatever you say. Down the hall. Cherri’s in room 28. She doesn’t get very many patrons so if she doesn't behave, well it’s not my problem. Don’t break her too much and don’t bother any of my other patrons.”

Not sparing you another glance, he went back to his phone.

You really didn’t want to spend any more time in his presence so you began your walk down the hallway. Just as dingy and gross as the lobby, the hallway also had the added bonus of being able to hear moans and the sound of skin against skin. You hurried forward, focused solely on the numbers stuck on the doors.

Finally, you arrived, the sounds of so many different people fucking seared in your brain. You allowed yourself a second to try and shake that memory out of your head before realizing you had no idea what course of action was common courtesy in this situation. I mean, you were given a key, but surely you weren’t supposed to just barge in, right? 

You decided to knock on the door as a way to announce your presence. 

“Come on in, hot stuff~” A high pitched voice purred. You took a deep breath and unlocked the door, no going back now.

You weren’t prepared for the sight that met you.

There, as promised, was Sans with a plump ecto body and a pink silk robe. He was sitting on the bed, one leg crossed over the other, the robe falling just far enough away to reveal a black, lacy lingerie set complete with stockings.

As he caught sight of you, his flirty grin faltered before coming back strained,

“Hello, beautiful,” he squeaked, desperately hoping you didn’t recognize him.

You made sure the door was locked behind you before turning back to him, a weak smile on your face,

“What are you doing here?” you asked softly.

Sans shifted, not so subtly using his robe to cover back up,

“I-I’m working, “ he whimpered, then, in a forced flirty tone, “Looking to have some fun with someone like you, beautiful~”

You made your way over and sat beside him,

“Sans-”

“Cherri.”

You blinked,

“What?”

“My name is Cherri. Call me Cherri,” he noticed your hesitation and continued quietly, dropping the falsetto for a moment, “ _Please_ Sweetheart.”

You relented, not being able to stand the pain and panic in his voice. The moment of weakness.

“Right. I-I’m, I’m sorry. _Cherri_ , if you needed money that bad, you should have come to me.” 

He shook his head, slowly circling his arms around himself in a hug,

“No.”

“Please S- Cherri! I want to help you.”

He stood up from the bed, hands clenched into fists,

“No! I don’t take handouts. San- Cherri the skeleton doesn’t take handouts. It’s my debt to pay, not yours. I- I won’t let you.”

So there you sat on the bed in that damn brothel, watching a single red tear roll down your friend’s face. Plan A was shot. You knew that. If there was one thing Sans was it was stubborn. Blindly, annoyingly stubborn. Time for plan B.

Pushing the frustration away, you took a deep breath and stood from the bed.

“Fine.”

Sans looked down at the floor, refusing to seem any weaker as he listened to the sound of your retreating footsteps. His eyes snapped back to meet yours when he heard you remove your coat and hang it on the rack by the door. He watched you also remove your shoes in bewilderment.

“What are you doing?”

“You refuse to accept my help and I refuse to let you go another day without it. So it’s not gonna be a handout, but you’re getting that money.”

“You don’t have to do this. I don’t want your pity,” he mumbled looking back down.

Smiling, you placed a hand under his chin and brought his head up to meet your gaze,

“I know. But maybe I want to,” his eyelights expanded in surprise so you continued, “Maybe I think you’re funny and attractive and sweet and you just gave me the opportunity to act on a crush I’ve had since I met you.”

Seeing only truth in my expression, he dropped the falsetto and managed a weak smile back at me,

“Doing things a little backwards, aren’t you sweetheart?”

You grinned wolfishly,

“Oh, I won’t be doing you backwards unless you ask really nicely.”

Having been caught off guard, Sans barked out a laugh at your dirty joke. The exaggerated movement brought to attention just how close you were. Bodies almost pressed up against each other and faces only inches apart.

“Before I do anything though,” I began, once again serious, “I need to make sure you want this too. Because you could tell me to leave right now and I would. I’d forget I ever saw you here and things would go back to normal. What happens next is completely up to you, Sans.”

His eyelights softened and his arms came up to wrap around your neck and pull you even closer. Your own hands moved to hold his hips.

“You ain’t the only one with a crush, Sweetheart.”

Suddenly, you were yanked even lower and you could taste Sans’ magic on your lips. Your eyes closed and suddenly all of your attention was focused on giving that skeleton the best kiss of his life.

Your mouths moved in sync, delicate skin never once getting caught on those sharp teeth of his. Soon enough, Sans’ mouth opened and his red tongue began prodding at your lips asking for entrance, you wasted no time in meeting his tongue with your own. You two fought for dominance, but ultimately you won, your tongue shooting forward to claim its new territory. Deciding you had enough of your hunched position, you picked Sans up by the hips, him automatically wrapping his legs around your waist and pulling the two of you even closer.

Eventually, you had to part, panting for air. His eyelights were blown wide and hazy at the edges and you were quite certain your expression wasn’t much better. 

“Damn,” he whispered, prompting you to let out a breathy giggle.

“Y’know,” you began, “Eventually I’d like to have access to those bones of yours, but for right now?” you squeezed his ass, “I’m really enjoying these thighs. Can’t wait to have them wrapped around my head.”

He grinned, flashing his golden tooth,

“I think someone is doing a little too much talking. C’mon Sweetheart, at this rate, I’ll die of old age before-ah!”

You shut him up by shoving your face into the crook of his neck and scraping your teeth against the bone peeking out from under the robe,

“Yeah, well, I think someone is wearing too many clothes,” you mumbled into his neck.

“Oh yeah?” You could practically hear the shit-eating grin in his voice, “Then do something about it.”

You didn’t need to be asked twice. Going in for another kiss, you walked him over to the bed and tossed him on it, climbing on above him. His robe fell open as he landed, revealing the lacy bra and panty set. Your mouth fell open as you took in the sight.

He rolled his eyes as you stayed there dumbfounded, and began taking his arms out of the sleeves,

“You’re hopeless.” 

“Hopeless? More like helpless,” you intertwined his fingers with yours and pinned his hands above him, “Sans, this right here is the single most attractive thing I have ever seen in my entire fucking life. Let me admire you a little bit.”

He quickly grew red in the face at your words while you bent down to begin kissing the ecto flesh along his sternum. 

“Shut up- no!” sputtered Sans, embarrassed, “Stop being such a softie and touch me already!”

You giggled into the soft flesh before raising your head to look at him,

“Isn’t that what I’m doing?”

“Sweetheart…” he warned,

You relented, removing your hands away from his own,

“Okay, okay. Keep your hands there for me, will you?”

His fingers twitched with the urge to disobey, but he kept them above his head, eyelights watching your every move.

With the increased mobility, you trailed your kisses lower. All the way down the sternum and the abdomen till you reached the waistband of his panties. His legs spread, revealing the wet spot in the crotch of his underwear. You looked back up at his face, only to be met with a smug wink. 

You grinned and skipped completely over his pelvis, opting instead to attack his thighs. He groaned, but before he could protest further, you pulled the crotch of his panties to the side, exposing his cunt to the cold air. You used your thumb to pull apart his outer labia, earning a soft hissing sound from him,

“You are such a fucking tease, Sweetheart,” he complained, throwing his head back.

You blew a soft stream of air on his exposed cunt and giggled,

“Oh, hush. You love it.”

He let out another impatient groan and you took that opportunity to give him exactly what he wanted. Very deliberately, you gave his slit a long, firm lick with the flat of your tongue. True to his chosen name, he did, in fact, taste a little bit like cherries. 

As you circled his clit with your tongue, he let out an adorable little moan and you couldn’t help but want to see what other sounds you could make come out of him.

You continued your ministrations until finally you decided that the panties in your way, as cute as they were, were way more trouble than they were worth. So you sat back on your heels, earning yourself a whine,

“Why the fuck would you stop?” he demanded. His face was flushed red and his eyelights were still hazy, but he wasn’t nearly wrecked enough for your tastes yet. 

“These,” you growled, sliding the garment in question down his hips, “are in my way.”

Without waiting for a response, you dove back in, propping his thighs over your shoulders and pulling them shut around your head as you worked. No longer having to worry about keeping a piece of fabric out of your way, you could now focus on doing more important things with your hands; like spreading his labia apart as you shoved your tongue inside of him.

Immediately you felt his fingers tangle in your hair as he let out an absolutely beautiful moan. Not really caring to chastise him at the moment for moving his hands, you let it slide and continued what you were doing, revelling in the way his back arched and his voice rose in pitch. His legs gradually wound tighter and tighter around your head. Sensing he was close, you planted your lips around his clit and gently sucked.

Like the snapping of a string, he came. A positively filthy moan ripped from his throat and the magic muscles in his legs tensed around your head, stiffening up and freezing in place. You continued the stimulation as he rode out his orgasm, only stopping when his legs began to relax and his hands relaxed their grip on your hair.

Easily pulling out of his limp grasp, you sat back on your heels and watched him come back to awareness. Despite being drawn to you, his eyelights were unbelievably fuzzy and unfocused. To your delight, they had taken the shape of little hearts. His ribcage heaved up and down, but you no longer bothered to question why a skeleton would need to breathe.

“I think,” his voice was noticeably hoarse as he sat up, “you’re the one wearing too many clothes.”

You let out a laugh, getting off the bed,

“Yeah, I think you might be right, Bones. How about I fix that?”

His gaze turned into something that seemed almost predatory as you began slowly unbuttoning your shirt. He watched with rapt attention, greedily drinking in every new inch of skin you uncovered for him. 

You thanked fuck that you had been prepared for plan B. While it wasn’t nearly as intricate or beautiful as the set Sans had been wearing, your bra and underwear at least matched. It matched, it was flattering, and it was the same colour as his magic which was a huge plus.

Slipping your shirt off of your arms, you let the garment fall to the floor. Then you turned all the way around so that your back was facing Sans and you slowly began working the pants over your hips and down your thighs. Making sure to bend over at the waist teasingly as you pushed the pants to the floor and stepped out of them. 

Now, only in your underwear, you turned to look back at Sans, whos expression was noticeably more predatory. Not gonna lie, it definitely made you feel more confident than before,

“Like what you see?” you asked, fully aware of the answer. He narrowed his eyes and unhooked his bra, throwing it on the floor with the rest of his garments without taking his red eyelights off you,

“Yer damn right sweetheart,” he opened his arms wide and you took the hint, wasting no time. As soon as you were in reach he tugged you down and flipped you onto the bed so that he towered over you.

On the way down you let out a surprised squeak before giggling at the hint of euphoria you felt once you realized what had happened. Sans only watched and as he leaned in closer the heart shapes of his eyelights became clearer and easier to see.

His intense loving gaze was the only thing keeping you from commenting on them,

“Yer absolutely gorgeous,” he whispered, bringing a blush to your face. His sudden softness caught you off guard. He leaned down to mumble into the sensitive skin on your neck, hot breath fanning over your skin, “You make me feel so good with that talented tongue of yours. With your soft hands. Your beautiful lips,” he leaned back to take in the view of your flushed face, his gaze turning predatory once again, “How’s about I return the favour, hmm? See what sounds I can pull out of those lips of yours? See if I can make you tremble and writhe?”

Your breath caught in your throat at the prospect. Not trusting your voice, you bit your lip and nodded. 

The next thing you knew, his mouth crashed to yours and you were kissing each other like it was the last thing you’d ever do. 

~~~~~~~~~

Bonus:

You and Papyrus were cooking for one of your hangouts. Well, he was cooking and you were doing your best to keep up as his assistant. Ever since Sans had told Papyrus that he had quit his job, Papyrus had been much less irritable and snippy. 

He spent more time in a good mood and held a new respect for you after you were able to convince Sans to stop going to his dangerous job. Of course, Sans was only able to do that because you paid off his debt, but Papyrus wasn’t aware of that and Sans made it clear he wanted to keep it that way.

Anyway, a byproduct of having the respect of Papyrus was that he paid attention to what you said and took what you wanted into account. Which is why you were currently helping Papyrus assemble your favourite dish instead of lasagna.

“Out of curiosity,” he began, breaking the comfortable silence that had fallen over you two as you cooked, “how did you convince my brother to quit? That stubborn dolt wouldn’t listen to me no matter what I did, so how did you get him to listen to you?”

Without thinking about what dumbass thing you were about to spew out of your mouth, you answered,  
“Ah, you know. I guess I’m just a cunning linguist.”

Immediately, you realized what you said and froze on the spot, your breath catching in your throat and your eyes wide.

Slowly you turned to look at Papyrus, desperately hoping something would save your ass. Hoping that maybe he didn’t hear or maybe he just wouldn’t know what you said. 

From the look on his face, you had no such luck. He looked all types of scandalized and disgusted as what you said processed in his brain.

You didn’t dare say anything else for fear of making the situation worse. 

“What the absolute fuck,” he finally responded. You shrunk into yourself, nervously awaiting his wrath,”I cannot believe you actually just alluded to having oral sex with my brother, what the fuck, human?!”

Out of the corner of your eye, you saw Sans take one step into the kitchen, see what was happening and immediately turn around and walk the other direction. Unfortunately for him so did Papyrus.

“Absolutely not! Sans get the fuck back here! You’re not getting out of this one so easily!”


End file.
